Product Name

  • Name

    Gibberellic acid

  • EINECS 201-001-0
  • CAS No. 77-06-5
  • Article Data10
  • CAS DataBase
  • Density 1.49 g/cm3
  • Solubility 5 g/L (20 °C) in water
  • Melting Point 227 °C
  • Formula C19H22O6
  • Boiling Point 628.6 °C at 760 mmHg
  • Molecular Weight 346.38
  • Flash Point 231.4 °C
  • Transport Information
  • Appearance white powder
  • Safety 26-36
  • Risk Codes 36
  • Molecular Structure Molecular Structure of 77-06-5 (Gibberellic acid)
  • Hazard Symbols IrritantXi
  • Synonyms Gibb-3-ene-1,10-dicarboxylic acid, 2,4a,7-trihydroxy-1-methyl-8-methylene-, 1,4a-lactone;4a,1-(epoxymethano)-7,9a-methanobenz[a]azulene-10-carboxylic acid, 1,2,4b,5,6,7,8,9,10,10a-decahydro-2,7-dihydroxy-1-methyl-8-methylene-13-oxo-;Activol GA;Monopotassium 2,4a,7-trihydroxy-1-methyl-8-methylenegibb-3-ene-1,10-dicarboxylate 1,4a-lactone, (1alpha,2beta,4aalpha,4bbeta,10beta)-;Gibberellic acid (GA3);2beta,4aalpha,7-Trihydroxy-1beta-methyl-8-methylene-4aalpha,4bbeta-gibb-3-ene-1alpha,10beta-dicarboxylic acid 1,4a-lactone;2,4a, 7-Trihydroxy-1-methyl-8-methylenegibb-3-ene-1,10-carboxylic acid 1-4-lactone;Pgr-iv;Monopotassium gibberellate;Gibrescol;GA3;Pro-Gibb Plus;Gibefol;Gib-Tabs;EPA Pesticide Chemical Code 043802;(1R,2R,5S,8S,9S,10R,11S,12S)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1(5,8).0(1,10).0(2,8)]heptadec-13-ene-9-carboxylic acid;Grocel;Acide gibberellique [ISO-French];Gibb-3-ene-1,10-dicarboxylic acid, 2,4a, 7-trihydroxy-1-methyl-8-methylene-, 1,4a-lactone, (1.alpha., 2.beta.,4a.alpha.,4b.beta.,10.beta.)-;Ralex;Regulex;Gibberellic acid ( GA3 );Giberillic acid;Gibberellic-acid;Gibberellic acid (GA3 );Activol;Gibberellins;EPA Pesticide Chemical Code 043801;2beta,4alpha,7-Trihydroxy-1-methyl-8-methylene-4aalpha,4bbeta-gibb-3-ene-1alpha,10beta-dicarboxylic acid 1,4a-lactone;Brellin;Gibberellic acid GA3;Ryzup;Gibb-3-ene-1,10-dicarboxylic acid, 2,4a,7-trihydroxy-1-methyl-8-methylene-, 1,4a-lactone, monopotassium salt, (1alpha,2beta,4aalpha,4bbeta,10beta)-;NCI-C55823;2,7-dihydroxy-1-methyl-8-methylene-13-oxo-1,2,4b,5,6,7,8,9,10,10a-decahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylic acid;Berelex;Gibberellin A3;2beta,4alpha,7-Trihydroxy-1-methylene-4aalpha,4bbeta-gibb-3-ene-1alpha,10beta-dicarboxylic acid 1,4a-lactone;Gib-Sol;Gibberellin X;Gibberellin;Gibberellinsaeure;Pro-Gibb;Release LC;Maxon (plant growth regulator);Gibberellins A4A7;Cekugib;Gibrofit;
  • PSA 104.06000
  • LogP 1.02710

Synthetic route

2β,4a,7-trihydroxy-1-methyl-8-methylene-gibb-3-ene-1α,10β-dicarboxylic acid 10,10'-anhydride 1->4a;1'->4'a-dilactone
19123-33-2

2β,4a,7-trihydroxy-1-methyl-8-methylene-gibb-3-ene-1α,10β-dicarboxylic acid 10,10'-anhydride 1->4a;1'->4'a-dilactone

A

GA3-7-alkohol
54878-53-4

GA3-7-alkohol

B

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

Conditions
ConditionsYield
With sodium tetrahydroborate; acetic acid In tetrahydrofuran for 0.5h; Yield given;A 72%
B n/a
With sodium tetrahydroborate; acetic acid In tetrahydrofuran for 0.5h; other conditions; Yields of byproduct given;A 72%
B n/a
gibberellin A3-ketone
5087-25-2, 58917-17-2

gibberellin A3-ketone

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

Conditions
ConditionsYield
With potassium dihydrogenphosphate; potassium tri-sec-butyl-borohydride
Diacetyl-gibberellinsaeure
19147-54-7, 65563-70-4

Diacetyl-gibberellinsaeure

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

Conditions
ConditionsYield
With sodium methylate In N,N-dimethyl-formamide at 23℃; for 4h;
gibberellin A5
561-56-8

gibberellin A5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

Conditions
ConditionsYield
With air; alpha-ketoglute dipotassium; potassium ascorbate; iron(II) sulfate In various solvent(s) at 30℃; for 2h; enzyme preparation from anthers of Oryza sativa L., pH 8.0; Yield given;
ent-7α-hydroxykaurene
53060-60-9

ent-7α-hydroxykaurene

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

Conditions
ConditionsYield
With Giberella fujikuroi at 25℃; for 24h; incubation;
0(3),0(13)-Diacetyl-gibberellin-A3-7-aldehyd
54878-55-6

0(3),0(13)-Diacetyl-gibberellin-A3-7-aldehyd

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: PDC / dimethylformamide / 3.5 h / 23 °C
2: NaOCH3 / dimethylformamide / 4 h / 23 °C
View Scheme
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

B

(4bR,7S,9aS,10R)-7-hydroxy-1-methyl-8-methylene-4b,6,7,8,9,10-hexahydro-5H-7,9a-methanobenzo[a]azulene-10-carboxylic acid
13613-87-1

(4bR,7S,9aS,10R)-7-hydroxy-1-methyl-8-methylene-4b,6,7,8,9,10-hexahydro-5H-7,9a-methanobenzo[a]azulene-10-carboxylic acid

Conditions
ConditionsYield
With sodium carbonate at 240℃; Product distribution; 1-5 min;A n/a
B 100%
With sodium carbonate at 240℃; 1-5 min;A n/a
B 100%
With hydrazine
acetic anhydride
108-24-7

acetic anhydride

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

Diacetyl-gibberellinsaeure
19147-54-7, 65563-70-4

Diacetyl-gibberellinsaeure

Conditions
ConditionsYield
With pyridine; dmap for 12h; Cooling with ice; Inert atmosphere;99%
With pyridine Ambient temperature;2.0 g
5-Hexen-1-ol
821-41-0

5-Hexen-1-ol

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

C25H32O6

C25H32O6

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; Inert atmosphere;99%
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

methyl iodide
74-88-4

methyl iodide

gibberellic acid methyl ester
510-50-9

gibberellic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In acetone98%
With potassium carbonate In acetone at 20℃; Inert atmosphere;95.4%
With potassium carbonate In acetone at 18℃; for 20h;94%
With potassium carbonate In acetone92%
With cesium fluoride In N,N-dimethyl-formamide for 24h; Ambient temperature;407 mg
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

dimethyl sulfate
77-78-1

dimethyl sulfate

gibberellic acid methyl ester
510-50-9

gibberellic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In acetone97%
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

ent-3α,13-dihydroxy-20-norgibberella-1(10),16-diene-7,19-dioic acid
19123-84-3

ent-3α,13-dihydroxy-20-norgibberella-1(10),16-diene-7,19-dioic acid

Conditions
ConditionsYield
With lithium; lithium diisopropyl amide In tetrahydrofuran; ammonia at -78℃;95%
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

C19H24O5
123592-49-4

C19H24O5

Conditions
ConditionsYield
With lithium In ethanol; ammonia at -78℃;93%
N-tert-butoxycarbonyl-O-diethylcarbamoyl-N-bromopropylhydroxylamine

N-tert-butoxycarbonyl-O-diethylcarbamoyl-N-bromopropylhydroxylamine

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

3-((tert-butoxycarbonyl)((diethylcarbamoyl)oxy)amino)propyl (1S,2S,4aR,4bR,7S,9aS,10S,10aR)-2,7-dihydroxy-1-methyl-8-methylene-13-oxo-1,2,4b,5,6,7,8,9,10,10a-decahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylate

3-((tert-butoxycarbonyl)((diethylcarbamoyl)oxy)amino)propyl (1S,2S,4aR,4bR,7S,9aS,10S,10aR)-2,7-dihydroxy-1-methyl-8-methylene-13-oxo-1,2,4b,5,6,7,8,9,10,10a-decahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃;93%
benzyl chloride
100-44-7

benzyl chloride

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

C26H28O6
1178-69-4

C26H28O6

Conditions
ConditionsYield
With potassium carbonate In acetone92%
acetic anhydride
108-24-7

acetic anhydride

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

C21H24O7

C21H24O7

Conditions
ConditionsYield
With pyridine; dmap at 20℃;91%
ethyldimethylsilyl chloride
6917-76-6

ethyldimethylsilyl chloride

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

C27H42O6Si2

C27H42O6Si2

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 0 - 25℃; Inert atmosphere;89%
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

gibberellin A3 3-O-palmitate

gibberellin A3 3-O-palmitate

Conditions
ConditionsYield
With pyridine for 15h; Ambient temperature;83%
triethylsilyl chloride
994-30-9

triethylsilyl chloride

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

C31H50O6Si2

C31H50O6Si2

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 0 - 25℃; Inert atmosphere;81%
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

(4bR,7S,9aS,10R)-7-hydroxy-1-methyl-8-methylene-4b,6,7,8,9,10-hexahydro-5H-7,9a-methanobenzo[a]azulene-10-carboxylic acid
13613-87-1

(4bR,7S,9aS,10R)-7-hydroxy-1-methyl-8-methylene-4b,6,7,8,9,10-hexahydro-5H-7,9a-methanobenzo[a]azulene-10-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride In water for 3h; Heating;78%
at 250 - 300℃; Product distribution;
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

C19H21IO6
127590-27-6

C19H21IO6

Conditions
ConditionsYield
With Iodine monochloride; sodium hydrogencarbonate In acetonitrile for 5h; Ambient temperature;77%
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

ent-2β,3α,13-trihydroxy-20-norgibberell-1(10),16-diene-7,19-dioic acid 19-2β-lactone

ent-2β,3α,13-trihydroxy-20-norgibberell-1(10),16-diene-7,19-dioic acid 19-2β-lactone

Conditions
ConditionsYield
With water; sodium hydroxide for 1.5h;77%
With tris(pentafluorophenyl)borate; benzo[1,3,2]dioxaborole In dichloromethane at 25℃; for 24h; Reagent/catalyst;
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

(4bS,7S,9aS,10R)-1,7-dimethyl-8-oxo-4b,6,7,8,9,10-hexahydro-5H-7,9a-methanobenzo[a]azulene-10-carboxylic acid
427-78-1

(4bS,7S,9aS,10R)-1,7-dimethyl-8-oxo-4b,6,7,8,9,10-hexahydro-5H-7,9a-methanobenzo[a]azulene-10-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride In water at 100℃; for 3h; Wagner-Meerwein Rearrangement;76.5%
With hydrogenchloride
Multi-step reaction with 2 steps
1: aqueous HCl
2: HCl
View Scheme
With hydrogenchloride In water for 2h; Reflux;
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride; water at 60℃;75%
With hydrogenchloride at 50℃;
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide
14227-90-8

2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide

gibberellin A3 α-L-(2,3,4,-tri-O-acetyl)arabinopyranosyl ester

gibberellin A3 α-L-(2,3,4,-tri-O-acetyl)arabinopyranosyl ester

Conditions
ConditionsYield
With Celite; silver carbonate In dichloromethane Heating;75%
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

A

GA3-7-alkohol
54878-53-4

GA3-7-alkohol

B

C32H44N2O6
58870-20-5

C32H44N2O6

Conditions
ConditionsYield
With sodium tetrahydroborate; dicyclohexyl-carbodiimide In tetrahydrofuran; 1,4-dioxane 1.) -15 deg C, 2.) 5 deg C, 12 h;A 74%
B 3%
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

(S)-oxiranemethanol
60456-23-7

(S)-oxiranemethanol

(1S,2S,4aR,4bR,7S,9aS,10S,10aR)-(R)-oxiran-2-ylmethyl 2,7-dihydroxy-1-methyl-8-methylene-13-oxo-1,2,4b,5,6,7,8,9,10,10a-decahydro-4a,1-(epoxymethano)-7,9amethanobenzo[a]azulene-10-carboxylate

(1S,2S,4aR,4bR,7S,9aS,10S,10aR)-(R)-oxiran-2-ylmethyl 2,7-dihydroxy-1-methyl-8-methylene-13-oxo-1,2,4b,5,6,7,8,9,10,10a-decahydro-4a,1-(epoxymethano)-7,9amethanobenzo[a]azulene-10-carboxylate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 6h;71%
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

C19H24O7
6800-32-4

C19H24O7

Conditions
ConditionsYield
With water; sodium hydroxide for 18h;66%
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
572-09-8

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

gibberellin A3 β-D-(2,3,4,6-tetra-O-acetyl)glucopyranosyl ester

gibberellin A3 β-D-(2,3,4,6-tetra-O-acetyl)glucopyranosyl ester

Conditions
ConditionsYield
With Celite; silver carbonate In dichloromethane Heating;63%
2,2,2-trifluorodiazoethane
371-67-5

2,2,2-trifluorodiazoethane

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

acetonitrile
75-05-8

acetonitrile

(1S,2S,4aR,4bR,7S,9aS,10S,10aR)-N-acetyl-2,7-dihydroxy-1-methyl-8-methylene-13-oxo-N-(2,2,2-trifluoroethyl)-1,2,4b,5,6,7,8,9,10,10a-decahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxamide

(1S,2S,4aR,4bR,7S,9aS,10S,10aR)-N-acetyl-2,7-dihydroxy-1-methyl-8-methylene-13-oxo-N-(2,2,2-trifluoroethyl)-1,2,4b,5,6,7,8,9,10,10a-decahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxamide

Conditions
ConditionsYield
With copper(l) iodide In toluene at 25℃; for 12h;62%
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside
3068-32-4

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

gibberellin A3 β-D-(2,3,4,6-tetra-O-acetyl)galactopyranosyl ester

gibberellin A3 β-D-(2,3,4,6-tetra-O-acetyl)galactopyranosyl ester

Conditions
ConditionsYield
With Celite; silver carbonate In dichloromethane Heating;61%
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

acetobromocellobiose
14227-66-8

acetobromocellobiose

Gibberellin A3 heptaacetylcellobiosylester
138866-62-3

Gibberellin A3 heptaacetylcellobiosylester

Conditions
ConditionsYield
With triethylamine In acetone for 16h; Ambient temperature;52%
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose
3068-31-3

1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose

gibberellin A3 β-D-(2,3,4,-tri-O-acetyl)xylopyranosyl ester

gibberellin A3 β-D-(2,3,4,-tri-O-acetyl)xylopyranosyl ester

Conditions
ConditionsYield
With Celite; silver carbonate In dichloromethane Heating;48%
(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride; water Wagner-Meerwein Rearrangement; Reflux;38%
With hydrogenchloride Heating;
terbium(III) nitrate hexahydrate

terbium(III) nitrate hexahydrate

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid
77-06-5

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

C38H46NO17Tb*4H2O

C38H46NO17Tb*4H2O

Conditions
ConditionsYield
With triethylamine In ethanol at 20℃;35%

Gibberellic Acid Chemical Properties

Empirical Formula: C19H22O6
Molecular Weight: 346.3744 
EINECS: 201-001-0 
Structure of Gibberellic Acid (CAS NO.77-06-5):

Index of Refraction: 1.661
Molar Refractivity: 85.786 cm3
Molar Volume: 231.972 cm3
Polarizability: 34.008 10-24cm3
Surface Tension: 71.863 dyne/cm
Density: 1.493 g/cm3
Flash Point: 231.438 °C
Enthalpy of Vaporization: 106.599 kJ/mol 
Melting Point: 227 °C
Boiling Point: 628.595 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25°C 
Storage temp: 0-6°C
Water Solubility: 5 g/L (20 º C) 
Stability: Stable. Combustible. Incompatible with acids, strong oxidizing agents. 
Product Categories: FINE Chemical & INTERMEDIATES; Plant Oils, Toxins, Phenolic Acids & Derivatives; Biochemistry; Plant Growth Regulators; Plant Growth Trgulators (Others); Antibiotic Explorer 
Synonyms of Gibberellic Acid (CAS NO.77-06-5): (1alpha,2beta,4aalpha,4bbeta,10beta)-2,4a,7-Trihydroxy-1-methyl-8-methylenegibb-3-ene-1,10-dicarboxylic acid 1,4a-lactone ; (3S,3aR,4S,4aS,7S,9aR,9bR,12S)-7,12-Dihydroxy-3-methyl-6-
methylene-2-oxoperhydro-4a,7-methano-9b,3-propenoazuleno(1,2-b)furan-4-carboxylic acid ; Activol ; Berelex ; Brellin ; CCRIS 4820 ; Caswell No. 467 ; Cekugib ; Gibberellin ; Gibberellin A3 ; Gibefol ; Gibrescol ; Gibreskol ; Grocel ; Pro-Gibb Plus ; Regulex ; Ryzup 

Gibberellic Acid Uses

 Gibberellic acid has the main following uses:

1.Gibberellic acid is a very potent hormone whose natural occurrence in plants controls their development. Since Gibberellic acid regulates growth, applications of very low concentrations can have a profound effect while too much will have the opposite effect. It is usually used in concentrations between 0.01-10 mg/L.
2.Gibberellic acid is a simple gibberellin, promoting growth and elongation of cells.

3.Gibberellic acid is sometimes used in laboratory and greenhouse settings to trigger germination in seeds that would otherwise remain dormant. It is also widely used in the grape-growing industry as a hormone to induce the production of larger bundles and bigger grapes, especially Thompson seedless grapes, and in the Okanagan and Creston Valley it is used in the cherry industry as a growth regulator.

Gibberellic Acid Toxicity Data With Reference

1.    

dnd-sal:spr 1 mmol/L

    PYTCAS    Phytochemistry. An International Journal of Plant Biochemistry. 11 (1972),3135.
2.    

dnd-mam:lym 1 mmol/L

    PYTCAS    Phytochemistry. An International Journal of Plant Biochemistry. 11 (1972),3135.
3.    

orl-mus TDLo:142 g/kg/78W-I:ETA

    NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) PB223-159 .
4.    

orl-rat LD50:6300 mg/kg

    85ARAE    Agricultural Chemicals, Books I, II, III, and IV. 3 (1976/77),43.

Gibberellic Acid Consensus Reports

EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

Gibberellic Acid Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36 
R36:Irritating to eyes.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.
WGK Germany: 3
RTECS: LY8990000
F: 10
HS Code: 29322980
Hazardous Substances Data 77-06-5(Hazardous Substances Data)
Mildly toxic by ingestion of gibberellic acid . It is showed to be questionable carcinogen by  experimental tumorigenic data.  When heated to decomposition it emits acrid smoke and irritating fumes.

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